JP2006528947A - ４”−置換マクロライド - Google Patents
４”−置換マクロライド Download PDFInfo
- Publication number
- JP2006528947A JP2006528947A JP2006529793A JP2006529793A JP2006528947A JP 2006528947 A JP2006528947 A JP 2006528947A JP 2006529793 A JP2006529793 A JP 2006529793A JP 2006529793 A JP2006529793 A JP 2006529793A JP 2006528947 A JP2006528947 A JP 2006528947A
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- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- oxo
- dihydro
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 50
- 208000015181 infectious disease Diseases 0.000 claims abstract description 7
- 230000000813 microbial effect Effects 0.000 claims abstract description 7
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 241001465754 Metazoa Species 0.000 claims abstract description 6
- 230000009885 systemic effect Effects 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 322
- 150000001875 compounds Chemical class 0.000 claims description 302
- -1 cyano, phenyl Chemical group 0.000 claims description 171
- 125000000217 alkyl group Chemical group 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 229960004099 azithromycin Drugs 0.000 claims description 92
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 77
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 229960002626 clarithromycin Drugs 0.000 claims description 39
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 21
- 229960003276 erythromycin Drugs 0.000 claims description 20
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 150000001540 azides Chemical class 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 363
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 244
- 239000000203 mixture Substances 0.000 description 169
- 239000000543 intermediate Substances 0.000 description 139
- 239000000243 solution Substances 0.000 description 131
- 239000011541 reaction mixture Substances 0.000 description 123
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 117
- 235000019439 ethyl acetate Nutrition 0.000 description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
- 230000002829 reductive effect Effects 0.000 description 89
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 85
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
- 239000010410 layer Substances 0.000 description 74
- 239000012044 organic layer Substances 0.000 description 67
- 239000000047 product Substances 0.000 description 63
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 61
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 60
- 239000002904 solvent Substances 0.000 description 57
- 239000007787 solid Substances 0.000 description 52
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 46
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 46
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
- 239000012043 crude product Substances 0.000 description 44
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000004440 column chromatography Methods 0.000 description 35
- 238000003756 stirring Methods 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 21
- 238000010898 silica gel chromatography Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000003480 eluent Substances 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000006196 drop Substances 0.000 description 13
- 238000004007 reversed phase HPLC Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- LZXCEBPGNFLHEQ-UHFFFAOYSA-N dibenzyl(2-chloroethyl)azanium;chloride Chemical compound Cl.C=1C=CC=CC=1CN(CCCl)CC1=CC=CC=C1 LZXCEBPGNFLHEQ-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 241000193996 Streptococcus pyogenes Species 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 241000606768 Haemophilus influenzae Species 0.000 description 4
- 241000588655 Moraxella catarrhalis Species 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000005826 halohydrocarbons Chemical class 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000007918 intramuscular administration Methods 0.000 description 4
- 238000007913 intrathecal administration Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000007922 nasal spray Substances 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 3
- IJSQTGSLZCKWJK-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidin-2-one;hydrochloride Chemical compound Cl.ClCCN1CCCC1=O IJSQTGSLZCKWJK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CC(CC(C(C1)C(C(C2)C(*=C)O)O)N2C2CC2)C1OCC[O+]CCC(O)O Chemical compound CC(CC(C(C1)C(C(C2)C(*=C)O)O)N2C2CC2)C1OCC[O+]CCC(O)O 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 241000193998 Streptococcus pneumoniae Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229940097362 cyclodextrins Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 3
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- RNTNZUJPGMYBFI-UHFFFAOYSA-M sodium;1-ethyl-6-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylsulfanyl]-4-oxoquinoline-3-carboxylate Chemical compound [Na+].CC(C)(C)OC(=O)NCCSC1=CC=C2N(CC)C=C(C([O-])=O)C(=O)C2=C1 RNTNZUJPGMYBFI-UHFFFAOYSA-M 0.000 description 1
- QTNIGDSAOBIWEZ-UHFFFAOYSA-M sodium;6-[2-(dibenzylamino)ethoxy]-1-ethyl-4-oxoquinoline-3-carboxylate Chemical compound [Na+].C=1C=C2N(CC)C=C(C([O-])=O)C(=O)C2=CC=1OCCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 QTNIGDSAOBIWEZ-UHFFFAOYSA-M 0.000 description 1
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0310984.0A GB0310984D0 (en) | 2003-05-13 | 2003-05-13 | Novel compounds |
| PCT/EP2004/005081 WO2004101585A1 (en) | 2003-05-13 | 2004-05-11 | Macrolides substituded at the 4'-position |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006528947A true JP2006528947A (ja) | 2006-12-28 |
| JP2006528947A5 JP2006528947A5 (zh) | 2007-06-28 |
Family
ID=9957982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006529793A Pending JP2006528947A (ja) | 2003-05-13 | 2004-05-11 | ４”−置換マクロライド |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20070213283A1 (zh) |
| EP (1) | EP1625137A1 (zh) |
| JP (1) | JP2006528947A (zh) |
| CN (1) | CN1820017A (zh) |
| AR (1) | AR044308A1 (zh) |
| CA (1) | CA2525449A1 (zh) |
| CL (1) | CL2004001007A1 (zh) |
| GB (1) | GB0310984D0 (zh) |
| WO (1) | WO2004101585A1 (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005108412A1 (en) * | 2004-05-06 | 2005-11-17 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Ester linked macrolides useful for the treatment of microbial infections |
| GB0424958D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424961D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| EP1879903A1 (en) | 2005-05-10 | 2008-01-23 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | Ether linked macrolides useful for the treatment of microbial infections |
| WO2009007988A1 (en) * | 2007-07-11 | 2009-01-15 | Alembic Limited | Process for the preparation of 6-o-methylerythromycin a 9-oxime |
| GB201520419D0 (en) * | 2015-11-19 | 2016-01-06 | Epi Endo Pharmaceuticals Ehf | Compounds |
| AU2020259997A1 (en) * | 2019-04-18 | 2021-11-25 | Azura Ophthalmics Ltd. | Compounds and methods for the treatment of ocular disorders |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5495585A (en) * | 1978-01-03 | 1979-07-28 | Pfizer | Oleandomycin*erythromycin and 4***deoxyy4*** alkyl amide derivative of erythromycin carbonate |
| JPS60231691A (ja) * | 1984-04-13 | 1985-11-18 | フアイザー・インコーポレーテツド | ９ａ‐アザ‐９ａ‐ホモエリスロマイシン誘導体 |
| US4686207A (en) * | 1985-11-12 | 1987-08-11 | Abbott Laboratories | Erythromycin A 11,12-carbonates and method of use |
| US5288709A (en) * | 1989-03-28 | 1994-02-22 | Abbott Laboratories | Erythromycin derivatives |
| WO1996034007A1 (es) * | 1995-04-27 | 1996-10-31 | Laboratorios Aranda, S.A. De C.V. | Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen |
| JPH11116593A (ja) * | 1997-08-06 | 1999-04-27 | Pfizer Prod Inc | Ｃ−４”置換マクロライド抗生物質 |
| JP2002502366A (ja) * | 1996-05-07 | 2002-01-22 | アボット・ラボラトリーズ | ３―デスクラジノース―２，３―無水エリスロマイシン誘導体 |
| WO2002032917A1 (en) * | 2000-10-19 | 2002-04-25 | Glaxo Group Limited | Macrolides |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| JP2005515978A (ja) * | 2001-11-14 | 2005-06-02 | グラクソ グループ リミテッド | マクロライド |
| JP2006506389A (ja) * | 2002-10-31 | 2006-02-23 | グラクソ グループ リミテッド | ４”修飾エリスロマイシン誘導体 |
-
2003
- 2003-05-13 GB GBGB0310984.0A patent/GB0310984D0/en not_active Ceased
-
2004
- 2004-05-11 CN CNA2004800196558A patent/CN1820017A/zh active Pending
- 2004-05-11 US US10/556,381 patent/US20070213283A1/en not_active Abandoned
- 2004-05-11 AR ARP040101613A patent/AR044308A1/es not_active Application Discontinuation
- 2004-05-11 CL CL200401007A patent/CL2004001007A1/es unknown
- 2004-05-11 WO PCT/EP2004/005081 patent/WO2004101585A1/en active Application Filing
- 2004-05-11 EP EP04732089A patent/EP1625137A1/en not_active Withdrawn
- 2004-05-11 CA CA002525449A patent/CA2525449A1/en not_active Abandoned
- 2004-05-11 JP JP2006529793A patent/JP2006528947A/ja active Pending
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5495585A (en) * | 1978-01-03 | 1979-07-28 | Pfizer | Oleandomycin*erythromycin and 4***deoxyy4*** alkyl amide derivative of erythromycin carbonate |
| JPS60231691A (ja) * | 1984-04-13 | 1985-11-18 | フアイザー・インコーポレーテツド | ９ａ‐アザ‐９ａ‐ホモエリスロマイシン誘導体 |
| US4686207A (en) * | 1985-11-12 | 1987-08-11 | Abbott Laboratories | Erythromycin A 11,12-carbonates and method of use |
| US5288709A (en) * | 1989-03-28 | 1994-02-22 | Abbott Laboratories | Erythromycin derivatives |
| WO1996034007A1 (es) * | 1995-04-27 | 1996-10-31 | Laboratorios Aranda, S.A. De C.V. | Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen |
| JP2002502366A (ja) * | 1996-05-07 | 2002-01-22 | アボット・ラボラトリーズ | ３―デスクラジノース―２，３―無水エリスロマイシン誘導体 |
| JPH11116593A (ja) * | 1997-08-06 | 1999-04-27 | Pfizer Prod Inc | Ｃ−４”置換マクロライド抗生物質 |
| WO2002032917A1 (en) * | 2000-10-19 | 2002-04-25 | Glaxo Group Limited | Macrolides |
| JP2004511566A (ja) * | 2000-10-19 | 2004-04-15 | グラクソ グループ リミテッド | マイクロライド |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| JP2005515978A (ja) * | 2001-11-14 | 2005-06-02 | グラクソ グループ リミテッド | マクロライド |
| JP2006506389A (ja) * | 2002-10-31 | 2006-02-23 | グラクソ グループ リミテッド | ４”修飾エリスロマイシン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070213283A1 (en) | 2007-09-13 |
| CL2004001007A1 (es) | 2005-03-18 |
| CA2525449A1 (en) | 2004-11-25 |
| WO2004101585A1 (en) | 2004-11-25 |
| CN1820017A (zh) | 2006-08-16 |
| EP1625137A1 (en) | 2006-02-15 |
| GB0310984D0 (en) | 2003-06-18 |
| AR044308A1 (es) | 2005-09-07 |
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